For 15 years now, a group of Los Angeles comedians has held a running poker club: Sarah Silverman is a member, as are Comedy Central roastmaster Jeffrey Ross, stoner comic Doug Benson and Henry Phillips. “I’m usually the butt of all the jokes,” says Phillips, a guitar-playing comedian. “I’m comfortable with that.”

So far, he’s parlayed his failure-prone persona into a darkly hilarious Web series and two movies, 2009’s “Punching the Clown” and its sequel, “Punching Henry,” out Friday in theaters and on demand now.

These people wanted to make a show about what a loser I was. And then, in typical loser fashion, the deal fell through.

Silverman appears in the new movie as a podcaster interviewing Phillips’ character — a mishap-enhanced version of himself — about his life as a touring comedian constantly set back by bad luck, bad decisions and hecklers. That catches the eye of TV executives (J.K. Simmons and Michaela Watkins) who aim to capitalize on Henry’s uncanny ability to screw up.

The last part, it turns out, isn’t far from reality. “After the first movie came out, we got a TV deal,” says Phillips. “And basically these people wanted to make a show about what a loser I was. And then, in typical loser fashion, the deal fell through.”

Nevertheless, it made for good material. “I’ve always found failure hilarious,” says Phillips. In his YouTube series, “Henry’s Kitchen,” he plays a single man in a lonely apartment who gives disastrous cooking lessons, enhanced by Phillips’ mournful musical accompaniment, credited to “Jose Suicidio.”

The genesis? YouTube itself. “It was 2011, the first movie had come out, and it was clear that it wasn’t going to be this huge launching point for my career, and I was going through a breakup,” says Phillips, now 47. “So I wanted to learn to cook. And on YouTube I found there’s an infinite number of amateur videos by these random guys, in a bachelor apartment or their mom’s attic, teaching you how to grill asparagus or something.” His first riff on the trope was made mainly to entertain his friends. The second installment, “How to Make Henry’s Anytime Chili For One,” found a wider audience, inspiring him to make more. Silverman has called it “the best cooking show ever,” and Mike Judge is such a fan, he signed on for a bit part in “Punching Henry.”

Every so often, Phillips says, someone tries to persuade him to bring “Henry’s Kitchen” to a bigger site. “It’s never been an attractive enough offer to get me to change,” he says. “They’re like, ‘You can get more exposure.’ I’m like, ‘Yeah, but this way I get to say ‘f–k’ whenever I want.”

As Henry puts it in the new film, “I think I’m failing very well doing what I love.”